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Home Blogs Tag: SISSY

Tag: SISSY

2009.10.12 23:36:02
Maid Stephanie

Sissy’s First Real Punishment

I have wanted to write to this all day and get out some of the new feelings I have had since the past weekend with my mistress. For the first time, I was really punished by my mistress. I know that with this lifestyle, the line between what is punishment and what is reward it blurred. I guess that in the end it is all reward and pleasurable or us sissy maids would not do it. But, what makes it overall pleasurable, is that along the way there are times when we truly are made to do things designed to make us physically or emotionally uncomfortable by someone who is taking control and dominating us. (And who overall cares for us) I think that this balance is the key to this type of relationship lasting and being equally beneficial for both partners both emotionally and physically. Up till this weekend, mistress Jade had not really punished me in a way that was definitely punishment. Till now, I had been what I would call disciplined. I have to do several rituals every day such as wear a chastity belt, recite a pledge and wear panties. I also rarely get to have orgasms.

This weekend, my mistress and I had a small spat about food preparation in the kitchen. We both made up and admitted we were both a little wrong and that was that. I had been hinting that I would not mind if she was more strict and to explore the realm of true punishment. I was about to be punished. My chosen punishment was to be locked in bondage and a large butt plug was to be inserted while I lay there alone for some set period of time. I was in the bedroom on the bed locked and plugged in no time. I heard the door shut and I was alone. I was left to my thoughts, and the feeling of the large intruder in my rectum with no contact and unable to move. I really didn’t like it. I felt very bad for misbehaving. Mistress came back after what seemed like an hour later. (It was really only 15 minutes)

I begged her forgiveness and begged for her to use her cock and let me lick her pussy to make up for my misgivings. I felt so submissive that I could hardly stand it. It would have been real added punishment if at that time she had not allowed my to please her sexually but she did. I craved to give her pleasure to somehow make up for being bad. I honestly cared about my pleasure less at that moment than I ever have. I was allowed to lick mistress’s wet pussy in various ways for a good long time. After mistress was nice and ready, I donned two condoms (One a numbing condom) and began to fuck my mistress with as much intensity as I could. She came several times during this session. Afterwards, I was directed to relock her property till next week.

This has opened up new avenues for both of us and I think my mistress senses this as well. I am excited to know that I can really be punished and trained to be her perfect sissy maid. Without the punishment part of this, I am not sure I could serve her as thoroughly and completely as I would like. I think it will also give both of us new ways to express our dominance and submissiveness. Mistress has already planned a session for next weekend to explore what activities will be classified as overall punishment, discipline, or pleasure within our relationship. I again am writing that I adore my mistress and just when I think things can’t possibly get any better, we discover a new avenue to explore and learn about. My mistress is amazing. If anyone reading this has just half the relationship me and mistress have, you will be smiling till your cheeks hurt everyday!



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2009.09.02 23:48:34
Maid Stephanie

I completed my shopping assignment tonight for my mistress. She text me specific items to be purchased in Victoria’s Secret for her to wear this weekend. I had to go by myself. I felt a little embarrassed going in by myself to purchase a bra and pantyhose. I felt so under her control even though she will not arrive till tomorrow.

I also had a dream last night that mistress was slowly giving me a hand job. The dream didn’t last long because of my waking up due to discomfort from my chastity belt. I know why I dreamed this. This week I have day dreamed about a sensation that didn’t last 3 seconds this past weekend. When I was unlocked for my mistress to use her cock, she applied a numbing cream prior to putting a numbing condom on just for good measure. When she applied the cream, I felt such rush of pleasure in my cock that I though I might have an orgasm right then. She applied the cream in a hand job type fashion. For just a few seconds it was heaven, then the sensation subsided and the numbness began. The condom ensured that I was going to last as long as mistress wanted me to. I was then able to focus fully on my Mistress’s pleasure and not be distracted by my own physical sensations. It is such an awesome feeling to sacrifice your physical pleasure so your mistress can experience more physical pleasure. I get a lot of pleasure, it is just more mental and less physical. I guess it is trading physical pleasure for mental pleasure, but you get much more mental pleasure than you gave up in physical sensations. This transference and selflessness is what I love about being locked up and being a sissy.



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2009.02.02 04:02:11
Levinia

I understand now that I was a selfish cross dresser, who used the dressing up as a game and all I really wanted was my own sexual pleasure. Starting in my teenage years and for more than 30 years, I dressed in female clothes and pretended to be Submissive, all just a game and while I could enjoy straight sex, it was much more fun for me if I was dressed up and acting as a sissy.

With the Internet, things got easy for me, lot's of women out there, lonely, divorced, widows and bored housewives. Most of them had never even heard of Sissies or Cross dressers, but most didn't have too many men asking them out either. So it was easy enough, take them out and have straight sex with them, then add a bit of bondage, a bit of role playing and then bring out the female clothes and let them meet Laura. I was always in control and it was just all about sex while dressed up.



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